CA2704981A1

CA2704981A1 - Aldh-2 inhibitors in the treatment of psychiatric disorders

Aldh-2 inhibitors in the treatment of psychiatric disorders Download PDF

Info

Publication number: CA2704981A1
Authority: CA; Canada
Prior art keywords: chromen; hydroxyphenyl; phenyl; methoxy; trifluoromethyl
Prior art date: 2007-11-06
Legal status : Abandoned

Application number

CA2704981A

Other languages

English (en)

French (fr)

Inventor

Ivan Diamond

David Overstreet

Current Assignee

Gilead Palo Alto Inc

Original Assignee

Individual

Priority date

2007-11-06

Filing date

2008-11-06

Publication date

2009-05-14

2008-11-06 Application filed by Individual filed Critical Individual

2009-05-14 Publication of CA2704981A1 publication Critical patent/CA2704981A1/en

Status Abandoned legal-status Critical Current

Links

239000003112 inhibitor Substances 0.000 title claims abstract description 25
208000020016 psychiatric disease Diseases 0.000 title claims abstract description 15
238000011282 treatment Methods 0.000 title description 20
208000019906 panic disease Diseases 0.000 claims abstract description 20
206010041250 Social phobia Diseases 0.000 claims abstract description 9
208000019116 sleep disease Diseases 0.000 claims abstract description 9
241000124008 Mammalia Species 0.000 claims abstract description 6
208000037870 generalized anxiety Diseases 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 264
-1 heteroaryl amide Chemical class 0.000 claims description 118
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 101
125000000217 alkyl group Chemical group 0.000 claims description 93
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
238000000034 method Methods 0.000 claims description 72
125000001072 heteroaryl group Chemical group 0.000 claims description 70
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 68
OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 58
239000001257 hydrogen Substances 0.000 claims description 58
229910052739 hydrogen Inorganic materials 0.000 claims description 58
125000003118 aryl group Chemical group 0.000 claims description 54
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
125000001424 substituent group Chemical group 0.000 claims description 51
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 48
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
125000003545 alkoxy group Chemical group 0.000 claims description 37
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
229910052736 halogen Inorganic materials 0.000 claims description 34
150000002367 halogens Chemical group 0.000 claims description 34
229910052760 oxygen Inorganic materials 0.000 claims description 34
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
125000004093 cyano group Chemical group *C#N 0.000 claims description 33
239000001301 oxygen Substances 0.000 claims description 33
208000019901 Anxiety disease Diseases 0.000 claims description 28
125000002947 alkylene group Chemical group 0.000 claims description 25
125000000623 heterocyclic group Chemical group 0.000 claims description 25
125000003342 alkenyl group Chemical group 0.000 claims description 24
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 23
125000000753 cycloalkyl group Chemical group 0.000 claims description 23
230000036506 anxiety Effects 0.000 claims description 22
125000000304 alkynyl group Chemical group 0.000 claims description 20
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
239000005711 Benzoic acid Substances 0.000 claims description 8
101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 8
ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 8
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
YYOOFJZTRCPVFD-UHFFFAOYSA-N 3-[[3-[4-(methanesulfonamido)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(O)=O)=CC=C2C1=O YYOOFJZTRCPVFD-UHFFFAOYSA-N 0.000 claims description 7
125000004193 piperazinyl group Chemical group 0.000 claims description 7
125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 6
XINYOLXTIGKVRM-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-oxo-2-[2-(trifluoromethyl)phenyl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)C=3C(=CC=CC=3)C(F)(F)F)=CC=C2C1=O XINYOLXTIGKVRM-UHFFFAOYSA-N 0.000 claims description 6
YEVVMGQTIHYLHJ-CYBMUJFWSA-N 7-[(1r)-1-[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound O([C@H](C)C=1ON=C(N=1)C=1C=C(C=C(F)C=1)C(F)(F)F)C(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 YEVVMGQTIHYLHJ-CYBMUJFWSA-N 0.000 claims description 6
FYMBTIMJLANAIU-UHFFFAOYSA-N 7-[[2-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O FYMBTIMJLANAIU-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Chemical group N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
BISVYANBIFBJIA-UHFFFAOYSA-N 2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)NC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O BISVYANBIFBJIA-UHFFFAOYSA-N 0.000 claims description 5
SKVYHLULOMUGKX-UHFFFAOYSA-N 2-fluoro-5-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC(F)=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=C(C(F)=CC=5)C#N)=CO4)=O)=CC=3)N=2)=C1 SKVYHLULOMUGKX-UHFFFAOYSA-N 0.000 claims description 5
UIUCEBUXYPDPAJ-UHFFFAOYSA-N 3-(3-acetylphenyl)-7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound CC(=O)C1=CC=CC(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=C(F)C=4)C(F)(F)F)C=C3OC=2)=O)=C1 UIUCEBUXYPDPAJ-UHFFFAOYSA-N 0.000 claims description 5
GFHOVQHRHREPPZ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(3-phenylpropoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCCC=3C=CC=CC=3)=CC=C2C1=O GFHOVQHRHREPPZ-UHFFFAOYSA-N 0.000 claims description 5
FXSYGQPEYZJTHI-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3OC(=NN=3)C=3C=NC=CC=3)=CC=C2C1=O FXSYGQPEYZJTHI-UHFFFAOYSA-N 0.000 claims description 5
GUZLXSMJFYJQFJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-4-yl-1,2,4-oxadiazol-3-yl)ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3N=C(ON=3)C=3C=CN=CC=3)=CC=C2C1=O GUZLXSMJFYJQFJ-UHFFFAOYSA-N 0.000 claims description 5
MGBNIYZXARWXHW-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(N=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O MGBNIYZXARWXHW-UHFFFAOYSA-N 0.000 claims description 5
JGOMKMRNUIOXIC-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O JGOMKMRNUIOXIC-UHFFFAOYSA-N 0.000 claims description 5
NXRZHVXCUDNZGL-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[6-(1h-pyrazol-5-yl)pyridin-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=NC(=CC=3)C3=NNC=C3)=CC=C2C1=O NXRZHVXCUDNZGL-UHFFFAOYSA-N 0.000 claims description 5
XAYXXBMMIHLDQI-UHFFFAOYSA-N 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=C1 XAYXXBMMIHLDQI-UHFFFAOYSA-N 0.000 claims description 5
JUCBBVFEJTVYFD-UHFFFAOYSA-N 4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O JUCBBVFEJTVYFD-UHFFFAOYSA-N 0.000 claims description 5
HSTCXSZUDZOKRP-UHFFFAOYSA-N 7-[2-(3-fluorophenyl)-2-oxoethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)C=3C=C(F)C=CC=3)=CC=C2C1=O HSTCXSZUDZOKRP-UHFFFAOYSA-N 0.000 claims description 5
RKGISUHWZBBCKR-UHFFFAOYSA-N 7-[2-[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3ON=C(N=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O RKGISUHWZBBCKR-UHFFFAOYSA-N 0.000 claims description 5
235000010233 benzoic acid Nutrition 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
PNNQLSVOFZVQDZ-HNNXBMFYSA-N n-[(1s)-1-(4-fluorophenyl)ethyl]-2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyacetamide Chemical compound N([C@@H](C)C=1C=CC(F)=CC=1)C(=O)COC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 PNNQLSVOFZVQDZ-HNNXBMFYSA-N 0.000 claims description 5
PMXLLFNDTDRGFI-UHFFFAOYSA-N n-[4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O PMXLLFNDTDRGFI-UHFFFAOYSA-N 0.000 claims description 5
WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims description 4
QXODMLJSSSYMLK-UHFFFAOYSA-N 2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-n-[2-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)NC=3C(=CC=CC=3)C(F)(F)F)=CC=C2C1=O QXODMLJSSSYMLK-UHFFFAOYSA-N 0.000 claims description 4
JUEBRUJMZIBZFF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O JUEBRUJMZIBZFF-UHFFFAOYSA-N 0.000 claims description 4
HEOQQDCLAMIWDE-UHFFFAOYSA-N 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzonitrile Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C#N)=CC=C2C1=O HEOQQDCLAMIWDE-UHFFFAOYSA-N 0.000 claims description 4
WCTAYNZYWWPMBP-UHFFFAOYSA-N 3-[[3-[4-(methanesulfonamido)phenyl]-4-oxochromen-7-yl]oxymethyl]benzamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(N)=O)=CC=C2C1=O WCTAYNZYWWPMBP-UHFFFAOYSA-N 0.000 claims description 4
FAHBJKISWFYSTG-UHFFFAOYSA-N 7-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=CC(F)=CC=3)=CC=C2C1=O FAHBJKISWFYSTG-UHFFFAOYSA-N 0.000 claims description 4
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
101100240527 Caenorhabditis elegans nhr-22 gene Proteins 0.000 claims description 4
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
PNNQLSVOFZVQDZ-OAHLLOKOSA-N n-[(1r)-1-(4-fluorophenyl)ethyl]-2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyacetamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)COC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 PNNQLSVOFZVQDZ-OAHLLOKOSA-N 0.000 claims description 4
IXNLDMMIZOOUOV-UHFFFAOYSA-N n-[4-[7-[(3-cyanophenyl)methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C#N)=CC=C2C1=O IXNLDMMIZOOUOV-UHFFFAOYSA-N 0.000 claims description 4
FIFFBIMRAZGZIN-UHFFFAOYSA-N n-[4-[7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1COC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(NS(C)(=O)=O)C=C1 FIFFBIMRAZGZIN-UHFFFAOYSA-N 0.000 claims description 4
QXYPVJQYTBVSBE-UHFFFAOYSA-N n-[4-[7-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=CC(F)=CC=3)=CC=C2C1=O QXYPVJQYTBVSBE-UHFFFAOYSA-N 0.000 claims description 4
RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 4
YARRGUWVCVLKCS-UHFFFAOYSA-N 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=N1 YARRGUWVCVLKCS-UHFFFAOYSA-N 0.000 claims description 3
QZQVAPKTAUQPCF-UHFFFAOYSA-N 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-N-methyl-1,3-oxazole-4-carboxamide Chemical compound CNC(=O)C1=COC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=N1 QZQVAPKTAUQPCF-UHFFFAOYSA-N 0.000 claims description 3
OESBYEICGXYNBT-UHFFFAOYSA-N 3-(4-aminophenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O OESBYEICGXYNBT-UHFFFAOYSA-N 0.000 claims description 3
MLHOACBDJNPKJC-UHFFFAOYSA-N 3-(4-aminophenyl)-7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O MLHOACBDJNPKJC-UHFFFAOYSA-N 0.000 claims description 3
ZJWNWERIHPKYCW-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(2-phenylethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3C=CC=CC=3)=CC=C2C1=O ZJWNWERIHPKYCW-UHFFFAOYSA-N 0.000 claims description 3
CTTKSJXFCLZWEY-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(2-piperazin-1-ylethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCNCC3)=CC=C2C1=O CTTKSJXFCLZWEY-UHFFFAOYSA-N 0.000 claims description 3
GABUIDRLSZLRFS-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(pyridin-2-ylmethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=CC=CC=3)=CC=C2C1=O GABUIDRLSZLRFS-UHFFFAOYSA-N 0.000 claims description 3
LYOPHGBGGFBIAP-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(pyridin-4-ylmethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=CN=CC=3)=CC=C2C1=O LYOPHGBGGFBIAP-UHFFFAOYSA-N 0.000 claims description 3
SGWYZMJMBDTNPE-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(3-phenyl-1,2,4-oxadiazol-5-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(N=3)C=3C=CC=CC=3)=CC=C2C1=O SGWYZMJMBDTNPE-UHFFFAOYSA-N 0.000 claims description 3
GQHHGMIEWPYQLZ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(N=3)C=3C=NC=CC=3)=CC=C2C1=O GQHHGMIEWPYQLZ-UHFFFAOYSA-N 0.000 claims description 3
FFXQJURUOMILQH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-phenyl-1,2,4-oxadiazol-3-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=CC=CC=3)=CC=C2C1=O FFXQJURUOMILQH-UHFFFAOYSA-N 0.000 claims description 3
NPDZVHPRRHSDIJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-pyridin-2-yl-1,2,4-oxadiazol-3-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3N=CC=CC=3)=CC=C2C1=O NPDZVHPRRHSDIJ-UHFFFAOYSA-N 0.000 claims description 3
AHYUTGIZIZIDKP-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-pyridin-2-yl-1,2-oxazol-3-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3N=CC=CC=3)=CC=C2C1=O AHYUTGIZIZIDKP-UHFFFAOYSA-N 0.000 claims description 3
BLMUWBUJDTZGQV-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-pyridin-3-yl-1,2,4-oxadiazol-3-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=NC=CC=3)=CC=C2C1=O BLMUWBUJDTZGQV-UHFFFAOYSA-N 0.000 claims description 3
XDBUTBAUTWQRHY-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=NC=CC=3)=CC=C2C1=O XDBUTBAUTWQRHY-UHFFFAOYSA-N 0.000 claims description 3
HKEWKJSYDITCPM-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-2-yl-1,2,4-oxadiazol-3-yl)ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3N=C(ON=3)C=3N=CC=CC=3)=CC=C2C1=O HKEWKJSYDITCPM-UHFFFAOYSA-N 0.000 claims description 3
AFPFBJUMGHWWSF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-3-yl-1,2,4-oxadiazol-3-yl)ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3N=C(ON=3)C=3C=NC=CC=3)=CC=C2C1=O AFPFBJUMGHWWSF-UHFFFAOYSA-N 0.000 claims description 3
HKXIGXKVBVSHLZ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[3-(trifluoromethyl)phenyl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O HKXIGXKVBVSHLZ-UHFFFAOYSA-N 0.000 claims description 3
PMIDRXUFPZSRBZ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(4-methoxyphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(OC)=CC=C1N1CCN(CCOC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)CC1 PMIDRXUFPZSRBZ-UHFFFAOYSA-N 0.000 claims description 3
YBRCUCDVZMFQDL-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O YBRCUCDVZMFQDL-UHFFFAOYSA-N 0.000 claims description 3
NLBVKHVFWSBBEC-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[5-(trifluoromethyl)-1h-pyrazol-4-yl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC3=C(NN=C3)C(F)(F)F)=CC=C2C1=O NLBVKHVFWSBBEC-UHFFFAOYSA-N 0.000 claims description 3
ZLHYZFVZAFHBEA-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[[3-(trifluoromethyl)phenyl]methylamino]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCNCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O ZLHYZFVZAFHBEA-UHFFFAOYSA-N 0.000 claims description 3
BXQJHBUPOKYULL-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[2-(3,4,5-trifluorophenyl)-1,3-oxazol-4-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=C(F)C(F)=C(F)C=3)=CC=C2C1=O BXQJHBUPOKYULL-UHFFFAOYSA-N 0.000 claims description 3
NVHXGZBXAVVPFO-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[2-[3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O NVHXGZBXAVVPFO-UHFFFAOYSA-N 0.000 claims description 3
XZZGBJWFXVPVMV-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-(2h-tetrazol-5-yl)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C=3NN=NN=3)=CC=C2C1=O XZZGBJWFXVPVMV-UHFFFAOYSA-N 0.000 claims description 3
CBQSSDNKQRPHMZ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-(trifluoromethyl)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O CBQSSDNKQRPHMZ-UHFFFAOYSA-N 0.000 claims description 3
IJKBDDMBAHSXDV-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]chromen-4-one Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1COC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 IJKBDDMBAHSXDV-UHFFFAOYSA-N 0.000 claims description 3
PHGCOEMZEZPYOR-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(3-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound COC1=CC=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)N=2)=C1 PHGCOEMZEZPYOR-UHFFFAOYSA-N 0.000 claims description 3
IUQDULUMXAXWBP-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O IUQDULUMXAXWBP-UHFFFAOYSA-N 0.000 claims description 3
DSNYSUDIVYIEQH-UHFFFAOYSA-N 3-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC(F)=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=C(C=CC=5)C#N)=CO4)=O)=CC=3)N=2)=C1 DSNYSUDIVYIEQH-UHFFFAOYSA-N 0.000 claims description 3
JNOYBALWQJYPES-UHFFFAOYSA-N 3-[[3-(4-aminophenyl)-4-oxochromen-7-yl]oxymethyl]benzamide Chemical compound NC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(N)=CC=4)=CO3)=O)=CC=2)=C1 JNOYBALWQJYPES-UHFFFAOYSA-N 0.000 claims description 3
WVKZSEGADHUEKE-UHFFFAOYSA-N 3-[[3-(4-aminophenyl)-4-oxochromen-7-yl]oxymethyl]benzonitrile Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C#N)=CC=C2C1=O WVKZSEGADHUEKE-UHFFFAOYSA-N 0.000 claims description 3
IMLRTJCRZHHKRW-UHFFFAOYSA-N 4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O IMLRTJCRZHHKRW-UHFFFAOYSA-N 0.000 claims description 3
XJKPZYKFZKQYCH-UHFFFAOYSA-N 4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC(F)=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=CC(=CC=5)C#N)=CO4)=O)=CC=3)N=2)=C1 XJKPZYKFZKQYCH-UHFFFAOYSA-N 0.000 claims description 3
QPSPVQPYOAKFBC-UHFFFAOYSA-N 4-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 QPSPVQPYOAKFBC-UHFFFAOYSA-N 0.000 claims description 3
YEVVMGQTIHYLHJ-ZDUSSCGKSA-N 7-[(1s)-1-[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound O([C@@H](C)C=1ON=C(N=1)C=1C=C(C=C(F)C=1)C(F)(F)F)C(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 YEVVMGQTIHYLHJ-ZDUSSCGKSA-N 0.000 claims description 3
ORRIPWVLGBZIDZ-UHFFFAOYSA-N 7-[2-(4-chlorophenoxy)ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCOC=3C=CC(Cl)=CC=3)=CC=C2C1=O ORRIPWVLGBZIDZ-UHFFFAOYSA-N 0.000 claims description 3
FAAGZNJVSVYNSW-UHFFFAOYSA-N 7-[2-(4-fluorophenyl)-2-oxoethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)C=3C=CC(F)=CC=3)=CC=C2C1=O FAAGZNJVSVYNSW-UHFFFAOYSA-N 0.000 claims description 3
XFAQSZLKVGZYAA-UHFFFAOYSA-N 7-[2-(4-fluorophenyl)ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3C=CC(F)=CC=3)=CC=C2C1=O XFAQSZLKVGZYAA-UHFFFAOYSA-N 0.000 claims description 3
KFKDUJLKVAOFQB-UHFFFAOYSA-N 7-[2-[2-(4-fluorophenyl)ethylamino]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCNCCC=3C=CC(F)=CC=3)=CC=C2C1=O KFKDUJLKVAOFQB-UHFFFAOYSA-N 0.000 claims description 3
HHONJABIGAPPKM-UHFFFAOYSA-N 7-[2-[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]propan-2-yloxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound N=1C(C=2C=C(C=C(F)C=2)C(F)(F)F)=NOC=1C(C)(C)OC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 HHONJABIGAPPKM-UHFFFAOYSA-N 0.000 claims description 3
JAGZCQBDQUBNEH-UHFFFAOYSA-N 7-[2-[4-(3-chlorophenyl)piperazin-1-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C=C(Cl)C=CC=3)=CC=C2C1=O JAGZCQBDQUBNEH-UHFFFAOYSA-N 0.000 claims description 3
KVDVZUSHUNMBDO-UHFFFAOYSA-N 7-[2-[4-(4-chlorophenyl)-1h-pyrazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3C(=CNN=3)C=3C=CC(Cl)=CC=3)=CC=C2C1=O KVDVZUSHUNMBDO-UHFFFAOYSA-N 0.000 claims description 3
SXFJOYLSGKZQEM-UHFFFAOYSA-N 7-[2-[4-(4-fluorophenyl)piperazin-1-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C=CC(F)=CC=3)=CC=C2C1=O SXFJOYLSGKZQEM-UHFFFAOYSA-N 0.000 claims description 3
CVHDDJFLECTRJK-UHFFFAOYSA-N 7-[2-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3OC(=NN=3)C=3C=CC(F)=CC=3)=CC=C2C1=O CVHDDJFLECTRJK-UHFFFAOYSA-N 0.000 claims description 3
KAJPBUYABCQBKK-UHFFFAOYSA-N 7-[2-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O KAJPBUYABCQBKK-UHFFFAOYSA-N 0.000 claims description 3
MKMPNJBMKLCURY-UHFFFAOYSA-N 7-[3-[2-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]propoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCCC=3N=C(OC=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O MKMPNJBMKLCURY-UHFFFAOYSA-N 0.000 claims description 3
PCKCUVRYWBKTEA-UHFFFAOYSA-N 7-[[2-(3,4-difluorophenyl)-1,3-oxazol-4-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=C(F)C(F)=CC=3)=CC=C2C1=O PCKCUVRYWBKTEA-UHFFFAOYSA-N 0.000 claims description 3
COLMHOKXSWZSER-UHFFFAOYSA-N 7-[[2-(3,5-difluorophenyl)-1,3-oxazol-4-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=C(F)C=C(F)C=3)=CC=C2C1=O COLMHOKXSWZSER-UHFFFAOYSA-N 0.000 claims description 3
JKGRQKQIEYBYTJ-UHFFFAOYSA-N 7-[[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=CC(Cl)=CC=3)=CC=C2C1=O JKGRQKQIEYBYTJ-UHFFFAOYSA-N 0.000 claims description 3
WEUVQMIOXQPDCT-UHFFFAOYSA-N 7-[[2-(4-fluorophenyl)-1,3-oxazol-4-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=CC(F)=CC=3)=CC=C2C1=O WEUVQMIOXQPDCT-UHFFFAOYSA-N 0.000 claims description 3
NFLMVGPBVSJOKQ-UHFFFAOYSA-N 7-[[3-fluoro-5-(trifluoromethyl)phenyl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O NFLMVGPBVSJOKQ-UHFFFAOYSA-N 0.000 claims description 3
MOSZHACXXNIKAF-UHFFFAOYSA-N 7-[[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C(=CC=CC=3)Cl)=CC=C2C1=O MOSZHACXXNIKAF-UHFFFAOYSA-N 0.000 claims description 3
GZQHEBGZIKUMDM-UHFFFAOYSA-N 7-[[5-(3-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(F)C=CC=3)=CC=C2C1=O GZQHEBGZIKUMDM-UHFFFAOYSA-N 0.000 claims description 3
BPVYYYUTPWPBES-UHFFFAOYSA-N 7-[[5-(3-fluorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=C(F)C=CC=3)=CC=C2C1=O BPVYYYUTPWPBES-UHFFFAOYSA-N 0.000 claims description 3
VQLYYLNXOIUOFU-UHFFFAOYSA-N 7-[[5-(4-chlorophenyl)-1,2-oxazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=CC(Cl)=CC=3)=CC=C2C1=O VQLYYLNXOIUOFU-UHFFFAOYSA-N 0.000 claims description 3
WMYIPPDFUUZWRA-UHFFFAOYSA-N 7-[[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=CC(F)=CC=3)=CC=C2C1=O WMYIPPDFUUZWRA-UHFFFAOYSA-N 0.000 claims description 3
TZRVABAXGZCOOH-UHFFFAOYSA-N 7-[[5-[2,5-bis(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C(=CC=C(C=3)C(F)(F)F)C(F)(F)F)=CC=C2C1=O TZRVABAXGZCOOH-UHFFFAOYSA-N 0.000 claims description 3
NPGQORNIHHVBJO-UHFFFAOYSA-N 7-[[5-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=CC=C2C1=O NPGQORNIHHVBJO-UHFFFAOYSA-N 0.000 claims description 3
CDZYCQRKIXMTJK-UHFFFAOYSA-N 7-[[5-[3,5-bis(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=CC=C2C1=O CDZYCQRKIXMTJK-UHFFFAOYSA-N 0.000 claims description 3
GVOQTGJRDTXIMR-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O GVOQTGJRDTXIMR-UHFFFAOYSA-N 0.000 claims description 3
CLFPJUWQTLWOEP-UHFFFAOYSA-N 7-[[5-[4-fluoro-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C(F)=CC=3)C(F)(F)F)=CC=C2C1=O CLFPJUWQTLWOEP-UHFFFAOYSA-N 0.000 claims description 3
229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 3
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
AAWXSHHENRRQRE-UHFFFAOYSA-N ethyl 1-[2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyethyl]pyrazole-4-carboxylate Chemical compound C1=C(C(=O)OCC)C=NN1CCOC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 AAWXSHHENRRQRE-UHFFFAOYSA-N 0.000 claims description 3
GKIIYMRXUSLEFZ-UHFFFAOYSA-N ethyl 4-[7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]-4-oxochromen-3-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=COC2=CC(OCC3=C(N=C(S3)C=3C=CC(=CC=3)C(F)(F)F)C)=CC=C2C1=O GKIIYMRXUSLEFZ-UHFFFAOYSA-N 0.000 claims description 3
IVLDGUKVQHCQCA-UHFFFAOYSA-N methyl 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-1,3-oxazole-4-carboxylate Chemical compound COC(=O)C1=COC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=N1 IVLDGUKVQHCQCA-UHFFFAOYSA-N 0.000 claims description 3
FKSRMBLWEXMUQH-UHFFFAOYSA-N methyl 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=C1 FKSRMBLWEXMUQH-UHFFFAOYSA-N 0.000 claims description 3
XCGPDNAYSXIGBN-UHFFFAOYSA-N methyl 3-[[3-[4-(hydroxymethyl)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(CO)=CC=4)=CO3)=O)=CC=2)=C1 XCGPDNAYSXIGBN-UHFFFAOYSA-N 0.000 claims description 3
GGWNBYMSLMPZCF-UHFFFAOYSA-N methyl 3-[[3-[4-(methanesulfonamido)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(NS(C)(=O)=O)=CC=4)=CO3)=O)=CC=2)=C1 GGWNBYMSLMPZCF-UHFFFAOYSA-N 0.000 claims description 3
ZPUAMDNSBAFJTB-UHFFFAOYSA-N n-(2,4-difluorophenyl)-4-[2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyethyl]piperazine-1-carboxamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C(=O)NC=3C(=CC(F)=CC=3)F)=CC=C2C1=O ZPUAMDNSBAFJTB-UHFFFAOYSA-N 0.000 claims description 3
IEHKIQDJTOPPTN-UHFFFAOYSA-N n-(3-fluorophenyl)-2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyacetamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)NC=3C=C(F)C=CC=3)=CC=C2C1=O IEHKIQDJTOPPTN-UHFFFAOYSA-N 0.000 claims description 3
SZCZFEMWSJXEAC-UHFFFAOYSA-N n-(3-fluorophenyl)-4-[2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyethyl]piperazine-1-carboxamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C(=O)NC=3C=C(F)C=CC=3)=CC=C2C1=O SZCZFEMWSJXEAC-UHFFFAOYSA-N 0.000 claims description 3
FNYQPJGJSIQOQK-UHFFFAOYSA-N n-[4-[4-oxo-7-[(2-phenyl-1,3-oxazol-4-yl)methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=CC=CC=3)=CC=C2C1=O FNYQPJGJSIQOQK-UHFFFAOYSA-N 0.000 claims description 3
ARHPCVRPEMHVFN-UHFFFAOYSA-N n-[4-[4-oxo-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O ARHPCVRPEMHVFN-UHFFFAOYSA-N 0.000 claims description 3
SCXVTUJUIPDVJB-UHFFFAOYSA-N n-[4-[7-[[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=CC(F)=CC=3)=CC=C2C1=O SCXVTUJUIPDVJB-UHFFFAOYSA-N 0.000 claims description 3
NJYMIOGEDYKFQY-UHFFFAOYSA-N n-[4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=C(F)C=4)C(F)(F)F)C=C3OC=2)=O)C=C1 NJYMIOGEDYKFQY-UHFFFAOYSA-N 0.000 claims description 3
YLOBJVZLCAELSS-UHFFFAOYSA-N prop-2-enyl 3-[3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-1,2,4-oxadiazol-5-yl]benzoate Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(=O)OCC=C)=CC=C2C1=O YLOBJVZLCAELSS-UHFFFAOYSA-N 0.000 claims description 3
FJZJXFQFHMJTSI-UHFFFAOYSA-N prop-2-enyl 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(=O)OCC=C)=CC=C2C1=O FJZJXFQFHMJTSI-UHFFFAOYSA-N 0.000 claims description 3
125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 2
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 2
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 2
VLRSADZEDXVUPG-UHFFFAOYSA-N 2-naphthalen-1-ylpyridine Chemical group N1=CC=CC=C1C1=CC=CC2=CC=CC=C12 VLRSADZEDXVUPG-UHFFFAOYSA-N 0.000 claims description 2
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical group C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 2
BCHLRGSTGMUSFO-UHFFFAOYSA-N 3-[[3-(4-aminophenyl)-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(O)=O)=CC=C2C1=O BCHLRGSTGMUSFO-UHFFFAOYSA-N 0.000 claims description 2
VFKSORDIMAUFFL-UHFFFAOYSA-N 4-(oxathian-3-yl)morpholine Chemical group O1SC(CCC1)N1CCOCC1 VFKSORDIMAUFFL-UHFFFAOYSA-N 0.000 claims description 2
GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical group C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 claims description 2
YBAAQOVRDFBILI-UHFFFAOYSA-N 7-[[5-(3,4-dichlorophenyl)-1,2-oxazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=C(Cl)C(Cl)=CC=3)=CC=C2C1=O YBAAQOVRDFBILI-UHFFFAOYSA-N 0.000 claims description 2
YYGCAYSDPMCHAO-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-methylsulfonylphenyl)chromen-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O YYGCAYSDPMCHAO-UHFFFAOYSA-N 0.000 claims description 2
RKVAGAXJZJFEDQ-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-[4-(hydroxymethyl)phenyl]chromen-4-one Chemical compound C1=CC(CO)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O RKVAGAXJZJFEDQ-UHFFFAOYSA-N 0.000 claims description 2
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
AMJINJSTVXQTMD-UHFFFAOYSA-N [4-[7-[[2-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methoxy]-4-oxochromen-3-yl]phenyl] dihydrogen phosphate Chemical compound C1=CC(OP(O)(=O)O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O AMJINJSTVXQTMD-UHFFFAOYSA-N 0.000 claims description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical group N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical group C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 2
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
CFXFFAFGWRNMJV-UHFFFAOYSA-N methyl 4-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 CFXFFAFGWRNMJV-UHFFFAOYSA-N 0.000 claims description 2
150000002916 oxazoles Chemical class 0.000 claims description 2
229950000688 phenothiazine Drugs 0.000 claims description 2
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
QVZCPNUNJCOGGA-UHFFFAOYSA-N propan-2-yl 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound CC(C)OC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=C1 QVZCPNUNJCOGGA-UHFFFAOYSA-N 0.000 claims description 2
CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical group N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 2
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical group N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 2
125000005505 thiomorpholino group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 6
125000001475 halogen functional group Chemical group 0.000 claims 5
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 1
DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims 1
QYQCFHLVHVSJTA-UHFFFAOYSA-N 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzonitrile Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C(=CC=CC=3)C#N)=CC=C2C1=O QYQCFHLVHVSJTA-UHFFFAOYSA-N 0.000 claims 1
NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims 1
DKTXNAYSCCZCGS-UHFFFAOYSA-N 2-trimethylsilylethyl 3-[[3-(3-cyanophenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound C[Si](C)(C)CCOC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=C(C=CC=4)C#N)=CO3)=O)=CC=2)=C1 DKTXNAYSCCZCGS-UHFFFAOYSA-N 0.000 claims 1
LNLIHPSCCYLOHF-UHFFFAOYSA-N 2-trimethylsilylethyl 3-[[3-(4-carbamoylphenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound C[Si](C)(C)CCOC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(=CC=4)C(N)=O)=CO3)=O)=CC=2)=C1 LNLIHPSCCYLOHF-UHFFFAOYSA-N 0.000 claims 1
CNFOIZLFPBENBM-UHFFFAOYSA-N 3-(3-fluorophenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound FC1=CC=CC(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=CC=4)C(F)(F)F)C=C3OC=2)=O)=C1 CNFOIZLFPBENBM-UHFFFAOYSA-N 0.000 claims 1
XUJUWOOYHUYKRF-UHFFFAOYSA-N 3-(4-aminophenyl)-7-[[3-(trifluoromethoxy)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3C=C(OC(F)(F)F)C=CC=3)=CC=C2C1=O XUJUWOOYHUYKRF-UHFFFAOYSA-N 0.000 claims 1
QVCQIPUPLJTJKR-UHFFFAOYSA-N 3-(4-aminophenyl)-7-[[3-(trifluoromethyl)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O QVCQIPUPLJTJKR-UHFFFAOYSA-N 0.000 claims 1
USHIWOJJGWWHKC-UHFFFAOYSA-N 3-(4-fluorophenyl)-7-[[5-(2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound COC1=CC=CC=C1C1=NC(COC=2C=C3C(C(C(C=4C=CC(F)=CC=4)=CO3)=O)=CC=2)=NO1 USHIWOJJGWWHKC-UHFFFAOYSA-N 0.000 claims 1
UNYJSYKAFBRDSF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-6-[[3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C(C(C1=C2)=O)=COC1=CC=C2OCC1=NC(C=2C=C(C=CC=2)C(F)(F)F)=NO1 UNYJSYKAFBRDSF-UHFFFAOYSA-N 0.000 claims 1
IGLFEFCJHYKGNJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-6-[[5-[4-methoxy-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-2-(trifluoromethyl)chromen-4-one Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C1=NC(COC=2C=C3C(=O)C(C=4C=CC(O)=CC=4)=C(OC3=CC=2)C(F)(F)F)=NO1 IGLFEFCJHYKGNJ-UHFFFAOYSA-N 0.000 claims 1
BTNOQJRRJASMJW-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(pyridin-3-ylmethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=NC=CC=3)=CC=C2C1=O BTNOQJRRJASMJW-UHFFFAOYSA-N 0.000 claims 1
MYLUNEORTANDOK-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(2-phenyl-1,3-oxazol-4-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=CC=CC=3)=CC=C2C1=O MYLUNEORTANDOK-UHFFFAOYSA-N 0.000 claims 1
YBSGKKITPLSUPH-FQEVSTJZSA-N 3-(4-hydroxyphenyl)-7-[(2s)-2-hydroxy-3-[[3-(trifluoromethyl)phenyl]methylamino]propoxy]chromen-4-one Chemical compound C([C@H](O)COC=1C=C2C(C(C(C=3C=CC(O)=CC=3)=CO2)=O)=CC=1)NCC1=CC=CC(C(F)(F)F)=C1 YBSGKKITPLSUPH-FQEVSTJZSA-N 0.000 claims 1
VIUAWBLQYVJXIW-IBGZPJMESA-N 3-(4-hydroxyphenyl)-7-[(2s)-2-hydroxy-3-phenylpropoxy]chromen-4-one Chemical compound C([C@@H](O)CC=1C=CC=CC=1)OC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 VIUAWBLQYVJXIW-IBGZPJMESA-N 0.000 claims 1
QPOMIYFFWNHPDD-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-phenyl-1,2-oxazol-3-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=CC=CC=3)=CC=C2C1=O QPOMIYFFWNHPDD-UHFFFAOYSA-N 0.000 claims 1
FPUFUYUDPHGFEH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3OC(=NN=3)C=3C=CN=CC=3)=CC=C2C1=O FPUFUYUDPHGFEH-UHFFFAOYSA-N 0.000 claims 1
XNRHIWZNASULGF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCOC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)CC1 XNRHIWZNASULGF-UHFFFAOYSA-N 0.000 claims 1
VOZPBFARGKFKDU-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(2-methylphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound CC1=CC=CC=C1N1CCN(CCOC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)CC1 VOZPBFARGKFKDU-UHFFFAOYSA-N 0.000 claims 1
GKDBURVCBFZSCD-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(3-methoxyphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound COC1=CC=CC(N2CCN(CCOC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)CC2)=C1 GKDBURVCBFZSCD-UHFFFAOYSA-N 0.000 claims 1
MVWFUJHZXMTRHS-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(3-methylphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound CC1=CC=CC(N2CCN(CCOC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)CC2)=C1 MVWFUJHZXMTRHS-UHFFFAOYSA-N 0.000 claims 1
STVSMLYUQNAJLH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(4-methylphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(C)=CC=C1N1CCN(CCOC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)CC1 STVSMLYUQNAJLH-UHFFFAOYSA-N 0.000 claims 1
KPWVMSRCNSRFBT-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-[2-(trifluoromethyl)phenyl]piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C(=CC=CC=3)C(F)(F)F)=CC=C2C1=O KPWVMSRCNSRFBT-UHFFFAOYSA-N 0.000 claims 1
HABMRRNWPZNAHB-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O HABMRRNWPZNAHB-UHFFFAOYSA-N 0.000 claims 1
QIMFQFMJFVNZFR-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-oxo-2-[4-(trifluoromethyl)phenyl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O QIMFQFMJFVNZFR-UHFFFAOYSA-N 0.000 claims 1
ZPUVRABODOBSAH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-(trifluoromethoxy)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(OC(F)(F)F)C=CC=3)=CC=C2C1=O ZPUVRABODOBSAH-UHFFFAOYSA-N 0.000 claims 1
XZWFEHFXGWFMKS-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-[3-(trifluoromethyl)phenyl]-1,2-oxazol-5-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(C=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O XZWFEHFXGWFMKS-UHFFFAOYSA-N 0.000 claims 1
VFUZTXQSDASORI-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound COC1=CC=CC=C1C(O1)=NN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 VFUZTXQSDASORI-UHFFFAOYSA-N 0.000 claims 1
RMXOJOGIANOTSJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(2-methylphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound CC1=CC=CC=C1C(O1)=NN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 RMXOJOGIANOTSJ-UHFFFAOYSA-N 0.000 claims 1
FUCKCJMQAGFLIF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound COC1=CC=CC(C=2OC(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)=NN=2)=C1 FUCKCJMQAGFLIF-UHFFFAOYSA-N 0.000 claims 1
SLDDEMWKXMOGSY-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(3-methylphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound CC1=CC=CC(C=2OC(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)=NN=2)=C1 SLDDEMWKXMOGSY-UHFFFAOYSA-N 0.000 claims 1
SCIHYFZNPVIOOQ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=NC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=NO1 SCIHYFZNPVIOOQ-UHFFFAOYSA-N 0.000 claims 1
VQAIBBQEMDSXGR-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound C1=CC(OC)=CC=C1C(O1)=NN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 VQAIBBQEMDSXGR-UHFFFAOYSA-N 0.000 claims 1
ZRCYZRQZQQCIAK-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound C1=CC(C)=CC=C1C(O1)=NN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZRCYZRQZQQCIAK-UHFFFAOYSA-N 0.000 claims 1
RKDOJVUCIUGPAG-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O RKDOJVUCIUGPAG-UHFFFAOYSA-N 0.000 claims 1
KRTVXOPDCMVMGC-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[4-methoxy-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C1=NC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=NO1 KRTVXOPDCMVMGC-UHFFFAOYSA-N 0.000 claims 1
YHHAYEWUUXQFOL-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[6-(trifluoromethyl)pyridin-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=NC(=CC=3)C(F)(F)F)=CC=C2C1=O YHHAYEWUUXQFOL-UHFFFAOYSA-N 0.000 claims 1
PKGVXZWMYVCZNT-UHFFFAOYSA-N 3-(4-methoxyphenyl)-7-[[5-(2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C(=CC=CC=3)OC)=CC=C2C1=O PKGVXZWMYVCZNT-UHFFFAOYSA-N 0.000 claims 1
RGQMOEXUFWMRLU-UHFFFAOYSA-N 3-(4-methylphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O RGQMOEXUFWMRLU-UHFFFAOYSA-N 0.000 claims 1
UZWQLFASQMHLAK-UHFFFAOYSA-N 3-[[2-hydroxy-3-[4-(methanesulfonamido)phenyl]-4-oxo-2,3-dihydrochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1C(=O)C2=CC=C(OCC=3C=C(C=CC=3)C(O)=O)C=C2OC1O UZWQLFASQMHLAK-UHFFFAOYSA-N 0.000 claims 1
YAAKJWVORLBNTF-UHFFFAOYSA-N 3-[[3-(4-carbamoylphenyl)-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(C(=O)N)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(O)=O)=CC=C2C1=O YAAKJWVORLBNTF-UHFFFAOYSA-N 0.000 claims 1
DDMANHXIYQTENK-UHFFFAOYSA-N 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-N-[[3-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(=O)NCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O DDMANHXIYQTENK-UHFFFAOYSA-N 0.000 claims 1
ATRDANSWHPMPDB-UHFFFAOYSA-N 3-[[3-(4-methylsulfonylphenyl)-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(O)=O)=CC=C2C1=O ATRDANSWHPMPDB-UHFFFAOYSA-N 0.000 claims 1
KFLSGMZNSZFNAJ-UHFFFAOYSA-N 4-[4-oxo-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=CC(=CC=5)C#N)=CO4)=O)=CC=3)N=2)=C1 KFLSGMZNSZFNAJ-UHFFFAOYSA-N 0.000 claims 1
VFRTZXWTORJKEU-UHFFFAOYSA-N 4-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzonitrile Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=CC(=CC=3)C#N)=CC=C2C1=O VFRTZXWTORJKEU-UHFFFAOYSA-N 0.000 claims 1
CXIIQPMREFANFO-UHFFFAOYSA-N 6-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)-2-(trifluoromethyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C(C(C1=C2)=O)=C(C(F)(F)F)OC1=CC=C2OCC1=NOC(C=2C=C(C=C(F)C=2)C(F)(F)F)=N1 CXIIQPMREFANFO-UHFFFAOYSA-N 0.000 claims 1
RPQZKJITPGRCKF-FQEVSTJZSA-N 7-[(2s)-2-hydroxy-3-[[3-(trifluoromethyl)phenyl]methylamino]propoxy]-3-(4-methoxyphenyl)chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(OC[C@@H](O)CNCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O RPQZKJITPGRCKF-FQEVSTJZSA-N 0.000 claims 1
BHESGBIBNPDUJW-FQEVSTJZSA-N 7-[(2s)-3-[(3,5-difluorophenyl)methylamino]-2-hydroxypropoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C([C@H](O)COC=1C=C2C(C(C(C=3C=CC(O)=CC=3)=CO2)=O)=CC=1)NCC1=CC(F)=CC(F)=C1 BHESGBIBNPDUJW-FQEVSTJZSA-N 0.000 claims 1
GUETZOYSPCKXKL-UHFFFAOYSA-N 7-[2-(4-fluorophenyl)-2-oxoethoxy]-3-(4-methoxyphenyl)chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(OCC(=O)C=3C=CC(F)=CC=3)=CC=C2C1=O GUETZOYSPCKXKL-UHFFFAOYSA-N 0.000 claims 1
KORFTUYYDNQLIT-UHFFFAOYSA-N 7-[2-[3-(5-bromopyridin-3-yl)-1,2,4-oxadiazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3ON=C(N=3)C=3C=C(Br)C=NC=3)=CC=C2C1=O KORFTUYYDNQLIT-UHFFFAOYSA-N 0.000 claims 1
YBMCDYRUWGLIEU-UHFFFAOYSA-N 7-[2-[4-(2-fluorophenyl)piperazin-1-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C(=CC=CC=3)F)=CC=C2C1=O YBMCDYRUWGLIEU-UHFFFAOYSA-N 0.000 claims 1
HOPUHQHIURDXAS-UHFFFAOYSA-N 7-[2-[4-(3-fluorophenyl)piperazin-1-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C=C(F)C=CC=3)=CC=C2C1=O HOPUHQHIURDXAS-UHFFFAOYSA-N 0.000 claims 1
LVBYYSGNQQWIJS-UHFFFAOYSA-N 7-[3-[(3,5-difluorophenyl)methylamino]-2-hydroxypropoxy]-3-(4-methoxyphenyl)chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(OCC(O)CNCC=3C=C(F)C=C(F)C=3)=CC=C2C1=O LVBYYSGNQQWIJS-UHFFFAOYSA-N 0.000 claims 1
TVYQUGOSXLQOGP-UHFFFAOYSA-N 7-[[3-(3-aminophenyl)-1,2,4-oxadiazol-5-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound NC1=CC=CC(C=2N=C(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)ON=2)=C1 TVYQUGOSXLQOGP-UHFFFAOYSA-N 0.000 claims 1
IBRIBDVVLALIBW-UHFFFAOYSA-N 7-[[3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]-3-[4-[[3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]phenyl]chromen-4-one Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(COC=3C=CC(=CC=3)C=3C(C4=CC=C(OCC=5ON=C(N=5)C=5C=C(C=CC=5)C(F)(F)F)C=C4OC=3)=O)ON=2)=C1 IBRIBDVVLALIBW-UHFFFAOYSA-N 0.000 claims 1
BYZRPKNYQMQCMK-UHFFFAOYSA-N 7-[[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(N=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O BYZRPKNYQMQCMK-UHFFFAOYSA-N 0.000 claims 1
WHBOOUQLMQINPB-UHFFFAOYSA-N 7-[[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=C(Cl)C=CC=3)=CC=C2C1=O WHBOOUQLMQINPB-UHFFFAOYSA-N 0.000 claims 1
VVVFLKUGSGNQNY-UHFFFAOYSA-N 7-[[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=CC(Cl)=CC=3)=CC=C2C1=O VVVFLKUGSGNQNY-UHFFFAOYSA-N 0.000 claims 1
WNYYVTUGJCLMLU-UHFFFAOYSA-N 7-[[6-(trifluoromethyl)pyridin-3-yl]methoxy]-3-[4-[[6-(trifluoromethyl)pyridin-3-yl]methoxy]phenyl]chromen-4-one Chemical compound C1=NC(C(F)(F)F)=CC=C1COC1=CC=C(C=2C(C3=CC=C(OCC=4C=NC(=CC=4)C(F)(F)F)C=C3OC=2)=O)C=C1 WNYYVTUGJCLMLU-UHFFFAOYSA-N 0.000 claims 1
YFTSDZIXAMNCEZ-UHFFFAOYSA-N [3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=C1 YFTSDZIXAMNCEZ-UHFFFAOYSA-N 0.000 claims 1
YZSKYZCRDKDSRB-UHFFFAOYSA-N [4-[7-[(3-methoxycarbonylphenyl)methoxy]-4-oxochromen-3-yl]phenyl]boronic acid Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(=CC=4)B(O)O)=CO3)=O)=CC=2)=C1 YZSKYZCRDKDSRB-UHFFFAOYSA-N 0.000 claims 1
NDJFEYMUZIFTRQ-UHFFFAOYSA-N [4-[7-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=CC(F)=CC=3)=CC=C2C1=O NDJFEYMUZIFTRQ-UHFFFAOYSA-N 0.000 claims 1
PVGOVCAOHGZDEF-UHFFFAOYSA-N [4-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]phenyl] propanoate Chemical compound C1=CC(OC(=O)CC)=CC=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 PVGOVCAOHGZDEF-UHFFFAOYSA-N 0.000 claims 1
VIICMKGBRBRXRG-UHFFFAOYSA-N [4-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 VIICMKGBRBRXRG-UHFFFAOYSA-N 0.000 claims 1
JSCZRVMYXMJBAJ-UHFFFAOYSA-N methyl 3-[7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]-4-oxochromen-3-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C(C3=CC=C(OCC4=C(N=C(S4)C=4C=CC(=CC=4)C(F)(F)F)C)C=C3OC=2)=O)=C1 JSCZRVMYXMJBAJ-UHFFFAOYSA-N 0.000 claims 1
FIAYNGLPHFJWNL-UHFFFAOYSA-N methyl 3-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=C(F)C=4)C(F)(F)F)C=C3OC=2)=O)=C1 FIAYNGLPHFJWNL-UHFFFAOYSA-N 0.000 claims 1
LMJMMPUNPQYONN-UHFFFAOYSA-N methyl 3-[[3-(4-acetyloxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(OC(C)=O)=CC=4)=CO3)=O)=CC=2)=C1 LMJMMPUNPQYONN-UHFFFAOYSA-N 0.000 claims 1
QMLJDJRQXXUTJD-UHFFFAOYSA-N methyl 3-[[3-[4-(2-amino-2-oxoethoxy)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(OCC(N)=O)=CC=4)=CO3)=O)=CC=2)=C1 QMLJDJRQXXUTJD-UHFFFAOYSA-N 0.000 claims 1
KHPANTWQMRVIHT-UHFFFAOYSA-N methyl 3-[[3-[4-(n'-hydroxycarbamimidoyl)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(=CC=4)C(N)=NO)=CO3)=O)=CC=2)=C1 KHPANTWQMRVIHT-UHFFFAOYSA-N 0.000 claims 1
FONJRTAJESCEPB-UHFFFAOYSA-N methyl 3-[[3-[4-[(4-methylphenyl)sulfonylamino]phenyl]-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(NS(=O)(=O)C=5C=CC(C)=CC=5)=CC=4)=CO3)=O)=CC=2)=C1 FONJRTAJESCEPB-UHFFFAOYSA-N 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
SZYSQGBOCVSYQS-UHFFFAOYSA-N n-(4-fluorophenyl)-4-[2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyethyl]piperazine-1-carbothioamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C(=S)NC=3C=CC(F)=CC=3)=CC=C2C1=O SZYSQGBOCVSYQS-UHFFFAOYSA-N 0.000 claims 1
KDHZOCWAWMYCJB-UHFFFAOYSA-N n-[3-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=C(F)C=4)C(F)(F)F)C=C3OC=2)=O)=C1 KDHZOCWAWMYCJB-UHFFFAOYSA-N 0.000 claims 1
IYWMHWZYYBEMLX-UHFFFAOYSA-N n-[4-[4-oxo-7-[[2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(SC=3)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O IYWMHWZYYBEMLX-UHFFFAOYSA-N 0.000 claims 1
XRXFUBQZEAXFBU-UHFFFAOYSA-N n-[4-[4-oxo-7-[[3-(trifluoromethoxy)phenyl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(OC(F)(F)F)C=CC=3)=CC=C2C1=O XRXFUBQZEAXFBU-UHFFFAOYSA-N 0.000 claims 1
DYOALZKAPRMVKL-UHFFFAOYSA-N n-[4-[4-oxo-7-[[3-(trifluoromethyl)phenyl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O DYOALZKAPRMVKL-UHFFFAOYSA-N 0.000 claims 1
OZIYZNIPBGCGKS-UHFFFAOYSA-N n-[4-[7-[2-[3-[2-fluoro-4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]ethoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCCC=3ON=C(N=3)C=3C(=CC(=CC=3)C(F)(F)F)F)=CC=C2C1=O OZIYZNIPBGCGKS-UHFFFAOYSA-N 0.000 claims 1
TULOYQLETVYVIG-UHFFFAOYSA-N n-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]-3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(=O)NCC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=C2C1=O TULOYQLETVYVIG-UHFFFAOYSA-N 0.000 claims 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
150000004866 oxadiazoles Chemical class 0.000 claims 1
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JCGPLQJNELWBFZ-UHFFFAOYSA-N propan-2-yl 3-[[3-(4-aminophenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound CC(C)OC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(N)=CC=4)=CO3)=O)=CC=2)=C1 JCGPLQJNELWBFZ-UHFFFAOYSA-N 0.000 claims 1
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